EP1464649A3 - Sugar derivatives comprising oxiranes or alpha,beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides - Google Patents

Sugar derivatives comprising oxiranes or alpha,beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides Download PDF

Info

Publication number
EP1464649A3
EP1464649A3 EP03398005A EP03398005A EP1464649A3 EP 1464649 A3 EP1464649 A3 EP 1464649A3 EP 03398005 A EP03398005 A EP 03398005A EP 03398005 A EP03398005 A EP 03398005A EP 1464649 A3 EP1464649 A3 EP 1464649A3
Authority
EP
European Patent Office
Prior art keywords
pesticides
preparation
oxiranes
utilisation
lactones
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP03398005A
Other languages
German (de)
French (fr)
Other versions
EP1464649A2 (en
EP1464649B1 (en
Inventor
Jorge Alberto Guerra Justino
Amélia Pilar grases santos Silva Reuter
Tana Lukeba Canda
Richard Wilkins
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Newcastle, The
Newcastle University of Upon Tyne
Instituto Politecnico De Santarem / Escola Superior Agraria
Universidade de Lisboa
Original Assignee
University of Newcastle, The
Newcastle University of Upon Tyne
Instituto Politecnico De Santarem / Escola Superior Agraria
Universidade de Lisboa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of Newcastle, The, Newcastle University of Upon Tyne, Instituto Politecnico De Santarem / Escola Superior Agraria, Universidade de Lisboa filed Critical University of Newcastle, The
Priority to EP09002251A priority Critical patent/EP2172473A1/en
Publication of EP1464649A2 publication Critical patent/EP1464649A2/en
Publication of EP1464649A3 publication Critical patent/EP1464649A3/en
Application granted granted Critical
Publication of EP1464649B1 publication Critical patent/EP1464649B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04Cyclic acetals
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/10Anhydrosugars, e.g. epoxides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/06Heterocyclic radicals

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Epoxy Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

The present invention relates to compounds of general formula (1): wherein R 1 and R 2 represent, independently from each other, hydrogen, halogen, alkoxy, substituted alkoxy or an ester group; R 3 represents -CH 2 R 6 (wherein R 6 represents an ester group), oxiranyl, or a group of formula wherein R 7 represents hydrogen or alkyl; R 9 represents phenyleulfanyl, phenylselenyl, phenylsulfoxy or phenyl-selenoxy; and R 9 represents hydrogen or halogen; as well as to the process for the preparation of these compounds, their utilization as pesticides and to the method to apply the same to the said pests or their locus.
EP03398005A 2003-04-03 2003-08-21 Sugar derivatives comprising oxiranes or alpha,beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides Expired - Lifetime EP1464649B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09002251A EP2172473A1 (en) 2003-04-03 2003-08-21 Alpha, beta-unsaturated, delta-lactones, process for their preparation and their application as pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PT10293503 2003-04-03
PT102935A PT102935A (en) 2003-04-03 2003-04-03 DERIVATIVES OF SUGAR CONTAINING CONTAINING OXYRANES OR ALPHA-LACTONES, BETA-INSATURATED, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS PESTICIDES

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP09002251.8 Division-Into 2009-02-18

Publications (3)

Publication Number Publication Date
EP1464649A2 EP1464649A2 (en) 2004-10-06
EP1464649A3 true EP1464649A3 (en) 2007-03-21
EP1464649B1 EP1464649B1 (en) 2010-10-20

Family

ID=32845219

Family Applications (2)

Application Number Title Priority Date Filing Date
EP09002251A Withdrawn EP2172473A1 (en) 2003-04-03 2003-08-21 Alpha, beta-unsaturated, delta-lactones, process for their preparation and their application as pesticides
EP03398005A Expired - Lifetime EP1464649B1 (en) 2003-04-03 2003-08-21 Sugar derivatives comprising oxiranes or alpha,beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP09002251A Withdrawn EP2172473A1 (en) 2003-04-03 2003-08-21 Alpha, beta-unsaturated, delta-lactones, process for their preparation and their application as pesticides

Country Status (4)

Country Link
EP (2) EP2172473A1 (en)
AT (1) ATE485301T1 (en)
DE (1) DE60334603D1 (en)
PT (1) PT102935A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7538139B2 (en) * 2004-07-30 2009-05-26 Instituto Politecnico De Santarem/Escola Superior Agraria Sugar derivatives comprising oxiranes or α, β-unsaturated γ-lactones, process for their preparation and their utilisation as pesticides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4994572A (en) * 1989-10-12 1991-02-19 Monsanto Company Synthesis of nojirimycin derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4994572A (en) * 1989-10-12 1991-02-19 Monsanto Company Synthesis of nojirimycin derivatives

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
A. VARGAS-BERENGUEL ET AL.: "Synthesis of 6-deoxyheptose derivatives via cyclic sulfates and oxetanes", SYNTHESIS, 1999, pages 1778 - 1786, XP002419336 *
A.P. RAUTER ET AL.: "Synthetic, fungicidal unsaturated gamma-lactones attached to furanosidic systems. Configurational determination by nuclear Overhauser effect", J. CARBOHYDRATE CHEM., vol. 14, 1995, pages 929 - 948, XP008033216 *
J. LEE ET AL.: "Conformationally constrained analogues of diacylglycerol. 13. Protein kinase C ligands based on templates derived from 2,3-dideoxy-L-erythro(threo)-hexono-1,4-lactone and 2-deoxyapiolactone", J. MED. CHEM., vol. 39, 1996, pages 4912 - 4919, XP002419334 *
PANFIL I ET AL: "1,3-DIPOLAR CYCLOADDITION OF NITRONES TO SUGAR ENLACTONES", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 47, no. 48, 1991, pages 10087 - 10094, XP002041211, ISSN: 0040-4020 *
R.D. EVANS, J.H. SCHAUBLE: "Synthesis of alfa-iodocarbonyl compounds using bis(sym-collidine)iodine(I) tetrafluoroborate/dimethyl sulfoxide", SYNTHESIS, 1986, pages 727 - 730, XP002419335 *
RAUTER A P ET AL: "Efficient synthesis of alpha,beta-unsaturated gamma-lactones linked to sugars", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 12, no. 8, 21 May 2001 (2001-05-21), pages 1131 - 1146, XP004245861, ISSN: 0957-4166 *
S. HANESSIAN ET AL.: "Mild and efficient preparation of gamma-substituted alfa, beta-unsaturated gamma-butyrolactones from epoxides", J. CHEM. SOC., CHEM. COMMUN., 1986, pages 754 - 755, XP002289672 *

Also Published As

Publication number Publication date
PT102935A (en) 2004-10-29
EP1464649A2 (en) 2004-10-06
ATE485301T1 (en) 2010-11-15
EP2172473A1 (en) 2010-04-07
DE60334603D1 (en) 2010-12-02
PT102935B (en) 2005-09-08
EP1464649B1 (en) 2010-10-20

Similar Documents

Publication Publication Date Title
WO2002020501A3 (en) Polyarylcarboxamides useful as lipid lowering agents
WO2001017973A3 (en) Novel herbicides
WO2001017972A3 (en) Novel herbicides
IL165502A0 (en) Method for preparing 3-halo-4,5-dihydro-1h-pyrazoles
AU2002317829A1 (en) Photostable organic sunscreen compounds with antioxidant properties and compositions obtained therefrom
CA2354880A1 (en) Method for the preparation of citalopram
WO1997047270A3 (en) Novel anti-viral compounds
AU1657100A (en) 4-trifluoromethyl-3-oxazolylpyridines, method for producing them, products containing the same, and their use as pesticides
WO2002079753A3 (en) 2-aminobenzoxazole derivatives and combinatorial libraries thereof
WO2000046210A3 (en) New process for preparing pesticidal intermediates
WO2004026224A3 (en) Process for preparing prostaglandin derivatives and starting materials for the same
WO2002016322A3 (en) Process for the preparation of 2-aminoethylpyridines
AU2002246317A1 (en) Novel glucopyranoside, process for isolation thereof, pharmaceutical composition containing same and use thereof
WO2002072567A3 (en) Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them
EP1464649A3 (en) Sugar derivatives comprising oxiranes or alpha,beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides
AU6578400A (en) Novel method for preparing benzoperhydroisoindole compounds
IT1293777B1 (en) PROCESS FOR THE PREPARATION OF TETRAAZAMACROCYCLES
YU3099A (en) Novel erythromycine derivatives, procedure for production and application thereof
WO2003064617A3 (en) Pestalotiopsis microsporia isolates and compounds derived therefrom
WO2000003975A3 (en) Aryl vinyl ether derivatives and their use as herbicides
WO1999048851A3 (en) Processes for preparing intermediates
CA2366600A1 (en) A process for the preparation of 1,4,7,10-tetraazacyclododecane
AU2003256091A1 (en) 1,2,4-triazole derivative, method for preparing the same, and pharmaceutical composition containing the same
EP1403260A3 (en) Optically active epoxy compounds and processes for their production
FR2823503B1 (en) NOVEL COMPOUNDS, MANUFACTURING METHOD, USE AS PIGMENTS AND COSMETIC COMPOSITION

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK

17P Request for examination filed

Effective date: 20070720

AKX Designation fees paid

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

17Q First examination report despatched

Effective date: 20080822

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REF Corresponds to:

Ref document number: 60334603

Country of ref document: DE

Date of ref document: 20101202

Kind code of ref document: P

REG Reference to a national code

Ref country code: NL

Ref legal event code: VDEP

Effective date: 20101020

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20110120

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20110221

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20110121

Ref country code: BE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20110131

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

26N No opposition filed

Effective date: 20110721

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 60334603

Country of ref document: DE

Effective date: 20110721

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110831

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20110821

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110831

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110831

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20120430

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 60334603

Country of ref document: DE

Effective date: 20120301

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110821

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110831

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110821

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20110821

Ref country code: CY

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20101020

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120301

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20101020